1,2-dichloro-3,3,3-trifluoropropene includes an unsaturated bond, and is expected to provide a function of a cleaner or a coolant as hydrochlorofluorocarbon (HCFC), which is relatively easily decomposed in the atmosphere.
There are various known methods for producing 1,2-dichloro-3,3,3-trifluoropropene. For example, A. L. Henne et al., J. Am. Chem. Soc., 1941, pp. 3478-3479 discloses a method of reacting 1,2,3,3,3-pentachloropropene with antimony trifluoride in a liquid-phase.
A. M. Whaley et al., J. Am. Chem. Soc., 1948, pp. 1026-1027 discloses a method of reacting 1,1,2,3,3-pentachloropropene with antimony trifluoride in a liquid phase by adding antimony pentachloride. R. N. Haszeldine et al., J. Chem. Soc., 1951, pp 2495-2504 discloses a method of adding potassium hydroxide in a solid state to 1,2,2,-trichloro-3,3,3-trifluoropropane in a liquid state and refluxing, while heating, the resultant substance to produce 1,2-dichloro-3,3,3-trifluoropropene.
Regarding a vapor-phase reaction, Japanese Laid-Open Patent Publication No. 2012-20992 discloses a method of producing a fluorine-containing propene represented by general formula, CF3CH═CHZ (Z is Cl or F), by a fluorination reaction and a dehalogenation reaction by use of a chlorine-containing compound as a material. In Example 4, it is described that 1,2-dichloro-3,3,3-trifluoropropene is generated as a byproduct of a fluorination reaction and a dehalogenation reaction of 1,1,1,3,3-pentachloropropane (240 fa).
According to the production method described in R. N. Haszeldine et al., J. Chem. Soc., 1951, pp 2495-2504, powdery potassium hydroxide is dispersed in 1,2,2-trichloro-3,3,3-trifluoropropane in a liquid state to cause a reaction. However, the yield is low (48%) and the reaction is not uniform. Therefore, this method is not considered to be efficient as an industrial production method.
As described in Japanese Laid-Open Patent Publication No. 2012-20992, it is known that 1,2-dichloro-3,3,3-trifluoropropene is generated by a fluorination reaction and a dehalogenation reaction of a chlorine-containing compound such as 1,1,1,3,3-pentachloropropane or the like in a vapor phase. However, it is difficult to obtain 1,2-dichloro-3,3,3-trifluoropropene in an industrially sufficient amount.
As can be seen from the above, it has been desired to establish a method for producing 1,2-dichloro-3,3,3-trifluoropropene, which is a target compound of the present invention, easily and in an industrial scale.